Some people chase fall foliage. Me? I chase those perfect Berkshire mornings when the mist floats between the hills like a spirit, and my hands wrap around a steaming mug of coffee from that tiny shop in Great Barrington. After a decade of fall adventures in the Berkshires, I still get butterflies when September rolls around
Sure, you could join the crowds up in Vermont, but here’s the thing about the Berkshires: it gets under your skin in the best possible way. Those winding back roads, the smell of woodsmoke, the way the maple leaves dance in the late afternoon light – it’s pure magic. After countless leaf-peeping adventures, here are my eight reasons why this hidden corner of Massachusetts should be your next fall escape. Fair warning: you might just fall in love like I did.

Table of Contents
My Favorite Fall Things to Do in the Berkshires (At a Glance)
There are countless things to do in the Berkshires in the fall, including farm festivals, apple picking, outdoor water sports, and of course, leaf peeping. Add to that the fall flair of colorful leaves and crisp autumn air, and you’ll see why people from around the world come to experience a Berkshires fall.
As a native Bostonian, I’ve had the chance to explore the Berkshires during different seasons. The fall months are my favorite, by far, because of the reasons above. But why choose the Berkshires over other places in New England? Get started with any of these sections below:
- Best Time to Visit – Peak foliage typically occurs between October 7-21.
- Scenic Fall Drives – Explore the Mohawk Trail, Jacob’s Ladder Scenic Byway, and Route 7 for breathtaking views.
- Top 8 Reasons to Visit in Fall – Why the Berkshires is a must-visit autumn destination.
- Charming New England Towns – Visit Lenox, Stockbridge, Great Barrington, and more.
- Cozy Inns & Lodging – Stay in Harbour House Inn, Chambery Inn, and other historic B&Bs.
- Must-Visit Museums – Discover the Norman Rockwell Museum, MASS MoCA, and Hancock Shaker Village.
- Farm-to-Table Dining – Savor local cider donuts, homemade pies, and fresh produce.
- Fall Festivals & Country Fairs – Enjoy the North Adams Fall Foliage Parade and Hancock Shaker Village Fair.
- Wellness Retreats – Relax at Miraval Berkshires, an all-inclusive retreat center.
- Epic Fall Hikes – Hike Mount Greylock, Monument Mountain, and Alford Springs.
- Best Apple Cider Donuts – Try Hilltop Orchards, Bartlett’s Orchard, and Taft Farms.
Click a link above to jump straight to that section and start planning your perfect fall trip to the Berkshires! 🍂✨
For more New England Fall inspiration, follow my adventures on Instagram: @Global.Viewpoint

Best time to visit the Berkshires in the fall
Looking to figure out when to see the fall foliage in the Berkshires? You can’t go wrong with a visit from late September through early November. However, the best time for leaf peeping is typically the second and third week of October.
At higher elevations, you can expect peak foliage in the Berkshires to be between October 7-14 while the lower elevations reaches their peak between October 14-21. It’s important to note that “peak foliage” means that 70% of the leaves are changing, so you’ll still find beautiful trees outside of that narrow window.
Read next: When is the best time to visit New England

Looking to do a fall foliage road trip? Read next: Ultimate Guide to Fall in New England
Scenic Fall Drives You Can’t Miss in the Berkshires
There’s something about driving through the Berkshires in the fall—the crisp air, the rolling hills painted in fiery reds and golds, and that perfect playlist humming in the background. If you want to experience New England’s autumn magic at its best, these three scenic routes will blow you away. Each offers stunning overlooks, hidden gems, and can’t-miss stops along the way.
1. Mohawk Trail (Route 2) – The Classic Leaf-Peeping Route 🍁
📍 Best For: Sweeping mountain views, historic sites, and a classic New England road trip feel
The Mohawk Trail, stretching 63 miles from Greenfield to North Adams, is one of New England’s oldest and most legendary scenic byways. Originally a Native American trade route, today it’s a leaf-peeper’s dream.
🍂 Must-See Stops Along the Mohawk Trail:
- Whitcomb Summit Overlook (Florida, MA) – One of the highest scenic viewpoints on the trail, offering panoramic views of rolling hills and fiery autumn foliage.
- Hairpin Turn Scenic Overlook (North Adams) – A thrilling switchback with a jaw-dropping view of the Hoosac Valley. At sunset, it’s pure magic.
- Natural Bridge State Park (North Adams) – Home to the only natural white marble bridge in North America, surrounded by vibrant fall colors.
- Bridge of Flowers (Shelburne Falls) – A charming pedestrian bridge lined with seasonal flowers and foliage, making for a perfect fall photo spot.
- Glacial Potholes (Shelburne Falls) – A fascinating natural wonder created by Ice Age meltwaters, framed by brilliant autumn leaves.
🍂 Best Time to Visit: Peak foliage is typically between October 7-14 at higher elevations and October 14-21 at lower elevations.
2. Jacob’s Ladder Scenic Byway (Route 20) – A Hidden Gem for Fall Colors 🍂
📍 Best For: A quieter, off-the-beaten-path drive with mountain views and charming villages
Jacob’s Ladder Scenic Byway (Route 20) is one of the Berkshires’ best-kept secrets. This 35-mile stretch between Lee and Chester winds through untouched forests, remote mountain passes, and small-town New England charm. If you want an uncrowded, peaceful leaf-peeping drive, this is it.
🍂 Must-See Stops Along Jacob’s Ladder:
- Becket Quarry (Becket, MA) – A hidden gem featuring abandoned granite quarries and peaceful forest trails surrounded by golden foliage.
- Keystone Arch Bridges Trail (Chester, MA) – A short, stunning hike leading to massive 19th-century stone railway bridges draped in vibrant fall colors.
- Chester-Blandford State Forest – Stop for hiking, picnicking, or a peaceful nature walk beneath a canopy of bright red and orange maple trees.
- October Mountain State Forest (Lee, MA) – The largest state forest in Massachusetts, offering miles of scenic drives, hiking trails, and panoramic views.
- Historic Chester Village – A charming New England town with white-steepled churches, antique shops, and an old-fashioned general store, all set against a backdrop of stunning fall foliage.
🍂 Best Time to Visit: Mid to late October, when the oak and maple forests hit their peak colors.
3. Route 7 – The Ultimate Berkshire Backroad 🍃
📍 Best For: Rolling farmland, historic inns, and peaceful countryside scenery
If you’re craving classic New England charm, Route 7 delivers. Running from Sheffield to Williamstown, this drive offers pastoral landscapes, quaint villages, and some of the best fall scenery in Massachusetts.
🍂 Must-See Stops Along Route 7:
- Bartholomew’s Cobble (Sheffield, MA) – A biodiversity hotspot with rolling meadows, rare trees, and breathtaking views of the Housatonic River in fall colors.
- Great Barrington Main Street – A picturesque small-town strip lined with boutique shops, cafés, and fall farmers’ markets.
- Stockbridge & The Red Lion Inn – One of the most iconic New England villages, home to the famous Red Lion Inn, Norman Rockwell Museum, and stunning fall scenery.
- Lenox Overlook – A quieter, lesser-known scenic stop where you can soak in sweeping views of the Berkshire hills.
- Mount Greylock State Reservation (Lanesborough, MA) – The highest peak in Massachusetts, offering a stunning 360-degree view of five states from the summit. The drive up is especially breathtaking in the fall.
🍂 Best Time to Visit: Early to mid-October, especially for higher-elevation spots like Mount Greylock.
Pro Tips for the Ultimate Fall Drive in the Berkshires:
✅ Go early or midweek – The Berkshires get busy on weekends. Sunrise drives offer empty roads and golden light for the best leaf-peeping experience.
✅ Pack a picnic – Many of these routes have scenic overlooks and hidden picnic spots where you can enjoy a fall-themed lunch.
✅ Take the backroads – Small detours off these main scenic drives will lead to hidden waterfalls, historic farms, and some of the best unspoiled views.
✅ Use a foliage tracker – Check the Massachusetts foliage report before heading out to catch the peak colors.
Whether you’re chasing the best fall views or just looking for a peaceful weekend escape, these scenic drives through the Berkshires will make your autumn road trip unforgettable. 🍂🚗✨
Now without further ado, let’s dive into all my favorite reasons to visit the Berkshires in the fall foliage months!
Top 8 Reasons to Visit the Berkshires in Fall
Here’s my ultimate guide on why you need to visit the Berkshires in the autumn of 2025:
1. Unspoiled nature and fun outdoor adventures
Located in scenic Western Massachusetts, the Berkshires is a hiker’s haven and a dilettante’s dream. During the autumn months, the entire region is bursting with intense fall foliage. Mountains and streams are covered by the flair of red and orange leaves – it’s a spectacular sight!
Perhaps one of the best vantage points is Massachusetts’ tallest mountain, Mount Greylock (3,489 ft.). From here, you can overlook 5 states on a clear day. In addition to the scenic drive up there, be sure to hike some of its trails along the Appalachian Trail.
Moreover, this time of year lends itself to exhilarating outdoor activities including kayaking, canoeing, and zip lining. One of my favorite memories from my recent trip was canoeing down the Housatonic River on a guided tour with Berkshire Canoe Tours. Hilary Bashara, who has owned this family-run tour for 20 years, is exceptionally knowledgeable and passionate about the local environment and community. It was wonderful paddling on a canoe, while learning about the wildlife and soaking in the fall ambiance around me.
Whether you’re an outdoor enthusiast or someone seeking a break from the hustle and bustle of the city, fall in the Berkshires will leave you in awe.
Read next: Top Hikes Across New England

2. Classic New England towns in the Berkshires
Looking for where to stay in the Berkshires this fall? The Berkshires is home to countless rural towns, each with their own cozy inns, farms, and restaurants. Here are some of my favorite towns and villages to visit in the fall, including lodging options:
Lee, Massachusetts
A small village in Berkshire County known for its cozy B&Bs and quaint New England architecture. It’s located right on the Massachusetts Turnpike, making it a great location between Boston and New York.

Best places to stay in Lee:
Cheap: $ | Black Swan Lee |
Mid: $$ | Chambery Inn |
Luxury: $$$ | Devonfield Inn |
Lenox
Lenox is a top resort town in the Berkshires. It’s home to Tanglewood, an annual music festival as well as many outdoor adventure activities. It boasts thousands of acres of beautiful nature, including forests, meadows, and mountains. But on a rainy day, you can check out many museums and historic sites in town as well.

Best places to stay in Lenox, MA:
Cheap: $ | Yankee Inn |
Mid: $$ | Seven Hills Inn |
Luxury: $$$ | 33 Main |
Pittsfield
For nature lovers, it doesn’t get much better than Pittsfield. This gorgeous fall town in the Berkshires is home to Pittsfield State Forest, which has over 11,000 acres of forest scenery and 30 miles of hiking trails. The town is also close to Hancock Shaker Village, one of the top hidden gems in New England.

Best places to stay in Pittsfield:
Cheap: $ | Berkshire Inn |
Mid: $$ | Berkshire Mountain Lodge |
Luxury: $$$ | Hotel on North |
North Adams
North Adams is a cultural hub in the Berkshires that’s home to the Mass MoCA Museum and Boston Symphony Orchestra. It’s also right on Route 7 and Route 2 (Mohawk Trail), which are two of the best scenic drives in the Berkshires for leaf peeping.
Best places to stay in and around North Adams:
Cheap: $ | Maple Terrace Motel |
Mid: $$ | The Porches Inn at Mass MoCA |
Luxury: $$$ | The Lodge @ America’s Switzerland |

Stockbridge
From colonial-era inns to unique attractions like the Norman Rockwell Museum and Berkshire Theater Festival, Stockbridge is a top destination in Berkshire County. It’s super close to Lenox and Lee, making it one of the best places to stay in the Berkshires in the fall.
Best places to stay in Stockbridge, MA:
Cheap: $ | The Red Lion Inn |
Mid: $$ | The Cottage B&B |
Luxury: $$$ | The Inn at Stockbridge |
Great Barrington
Located in the southern part of the Berkshires near Connecticut, Great Barrington is another great place to stay in the Berkshires for fall colors. It’s just a short drive to many beautiful spots, including Bash Bish Falls, Housatonic Flats Reserve, and Fountain Pond State Park. This makes it a gateway to the many nature destinations in the region.

Best places to stay in Great Barrington:
Cheap: $ | The Briarcliff Motel |
Mid: $$ | Granville House |
Luxury: $$$ | Wainwright Inn |
3. Charming inns
In the Berkshires, you’ll find many warm and welcoming B&Bs that each have their own unique story, vibe, and décor. Among these intriguing guest houses, I was particularly impressed with the Harbour House Inn and Chambery Inn.
Harbour House Inn
Built in 1793, the Harbour House Inn is a historic, colonial-style home that embodies the charm of the Berkshires. Each of its 6 guest rooms offer an enchanting ambiance and all the amenities for a comfortable stay.
Each morning, the innkeeper, Jen Showalter, concocts a hearty gourmet breakfast using delicious local ingredients! One of my fondest memories from the Inn was spending breakfast conversing with fellow guests over interesting current events. Given our busy, hurried lifestyles, I feel that a friendly breakfast setting presents a wonderful opportunity to engage with our peers.

Chambery Inn is another top place to stay in the Berkshires in the fall
Another inn that embodies the spirit of fall in the Berkshires is the Chambery Inn. Once a 19th-century schoolhouse, the Chambery Inn is a French-inspired B&B with 9 spacious suites. Each room is equipped with a fireplace and whirlpool tub, perfect for rest and relaxation!
One of my favorite experiences at the Chambery Inn was its homemade breakfast. Every morning, the innkeepers deliver a breakfast basket to each room— the best way to start the day.
Particularly during the stunning autumn months, each of these inns offer a unique lodging experience in the heart of the Berkshires!

4. Captivating museums
On a rainy fall day in the Berkshires, you won’t have to twiddle your thumbs or risk water damaging your camera. Instead, hop into one of the region’s many museums and learn about the heritage behind this beautiful destination.

Top fall activities in the Berkshires for museum lovers
For those seeking a dose of art, culture, and history in their next vacation, look no further than the Berkshires! During my visit, I stopped by several museums that each had something special to offer. At the Norman Rockwell Museum, it was fascinating to learn about Norman Rockwell’s magnificent artwork and legacy on American history. From “The Four Freedoms” to “Home for Christmas”, Rockwell’s collection is truly an artistic inspiration.
It was also a pleasure checking out the Massachusetts Museum of Contemporary Arts (Mass MoCA) in North Adams. This factory-turned-art-museum is one of the largest contemporary art galleries in the United States. Much of the visual art on display is edgy and eccentric, which makes for a thought-provoking and unconventional experience.
My favorite museum of all is the Hancock Shaker Village in Pittsfield. Established in 1791, Hancock Shaker Village is a historic landmark and museum that offers a glimpse of the simple and rustic lifestyles of the Shakers. Similar to the Quakers, the Shakers were a Christian sect that passionately practiced pacifism, equality, and sustainability.
Inside this village, you’ll find historic buildings and artifacts, handicraft exhibitions, and farm animals that bring the Shaker community to life. Whether you’re planning a weekend trip or extended getaway to the Berkshires, make sure these museums are on your list!

5. The Berkshires is praised for its farm-to-table dining.
What better way to experience a new place than through its food? With the autumn harvest in full swing, fall in the Berkshires is a great time to eat your way through its amazing restaurants.
After a long day exploring the fall foliage, it’s nice to stop by local restaurants and diners for a taste of the local cuisine. One thing that the Berkshires does extraordinarily well is farm-to-table dining. Many restaurants and B&Bs integrate locally-sourced ingredients into their menus, which come from the fall harvest. Cider donuts, anyone?
In particular, I was impressed by Trail House Kitchen in North Adams. Named after the nearby Appalachian and Mohawk trails, Trail House Kitchen is a family-run restaurant with a beautiful outdoor patio and delicious comfort food. My favorite dishes were the beef medallions and pomegranate cheesecake, which were truly out of this world!
In addition to trying dishes at local restaurants and cafes, I also made the obligatory stop to Chocolate Springs Café in Lenox. This confectionery shop is a chocolate lover’s dream. I’d even argue that it produces some of the finest chocolate in the world. As a self-proclaimed chocolate connoisseur, I was most impressed by the hot chocolate and passion fruit chocolate bars. After endless sightseeing in the Berkshires, a tasty treat is much needed.

6. Country fairs and other special events
There’s always something exciting happening in the Berkshires, especially during the fall months.
Locals and visitors alike are drawn to the region for its festivals and fairs. Here are some of the popular ones you can’t miss:
– North Adams Fall Foliage Parade: A day of family fun, including a children’s fair, road race, craft fair, and various performances.
– Berkshire Botanical Garden Harvest Festival: One of the region’s largest autumn festivals. More than 100 artisan vendors are in attendance, in addition to families who come for the live entertainment, hay rides and games, and other farm-based activities. children’s activities.
– Hancock Shaker Village Country Fair: A popular event where local farmers and artisans bring a festive fall atmosphere to this historic village.
– Hawthorne Valley Fall Festival: A free public event brimming with live music, local food and artisan goods, apple cider pressing, and hay rides.
7. The Berkshires is home to a wellness retreat like no other
Are you into wellness retreats? The Berkshires is home to one of the coolest wellness resorts in the country, Miraval Berkshires. It’s an all-inclusive, where you can choose from hundreds of unique experiences, including meditation and yoga sessions, archery, obstacles courses, and spa visits. In the winter, you can even do cold immersion here, which is a huge plus for Wim Hoffers like myself.

After a long day of chasing the fall colors around the Berkshires, I can’t imagine a better place to relax and unwind. It’s truly one of the coolest retreat centers worldwide. Visiting Miraval is undoubtedly among the top things to do in the Berkshires in the fall.
Read next: Miraval Berkshires Resort Review

8. Relaxation and inspiration in the Berkshires
Aside from its activities and attractions, the Berkshires fosters a serene atmosphere perfect for relaxation.
As you’re gazing at the fall foliage and dramatic landscapes, it’s easy to disconnect from your otherwise busy lifestyle and live (and feel) in the moment. Feeling the cool, gentle breeze as the vibrant-colored leaves sway in the air. Waking up every morning to the smell of livestock and birds chirping. Taking a deep breath and feeling inspired by the stunning scenery. These are some of the surreal experiences that will draw you to the Berkshires, year after year.
Especially during the fall foliage season, you will feel enlivened by the natural beauty and deep serenity of the Berkshires.
Epic Fall Hikes in the Berkshires
There’s no better way to experience the brilliant fall foliage of the Berkshires than by hitting the trails. The region’s mix of rolling hills, rugged peaks, and untouched forests bursting with autumn colors makes it a paradise for hikers. Whether you’re looking for a challenging summit trek or a peaceful woodland stroll, these three hikes offer some of the most jaw-dropping fall views in Massachusetts.
1. Mount Greylock via Stony Ledge – The Most Iconic View in the Berkshires 🏔️🔥
📍 Location: Mount Greylock State Reservation, Lanesborough, MA
📏 Distance: 4.5 miles round trip (moderate) OR 1.3 miles from Sperry Road
📈 Elevation Gain: 1,000 feet
⌛ Time Needed: 2-3 hours
Why It’s Epic in the Fall:
Mount Greylock is the highest peak in Massachusetts (3,489 ft.), and in autumn, it delivers some of the most breathtaking views in New England. The Stony Ledge trail is a lesser-known gem that provides an incredible panoramic overlook without the steep, crowded summit climb.
🍂 Must-See Highlights:
- Stony Ledge Overlook – A mind-blowing viewpoint with 360-degree views of the Taconic and Green Mountains painted in deep reds, oranges, and yellows.
- Mount Greylock Summit – If you’re up for an extra challenge, extend your hike to the top of the mountain, where you’ll find the famous Veterans War Memorial Tower and a view stretching across five states.
- Bascom Lodge – A cozy, rustic lodge at the summit offering hot apple cider and warm meals (open through mid-October).
🍁 Best Time to Hike: Mid-October for peak foliage at higher elevations.
🚗 Pro Tip:
- For an easier route, you can drive up to Sperry Road Campground and do a short 1.3-mile round trip hike to Stony Ledge.
- If you want a longer adventure, consider hiking from the Mount Greylock Visitor Center (6.6 miles round trip).
2. Monument Mountain – The Most Scenic Short Hike 🏞️🍁
📍 Location: Great Barrington, MA
📏 Distance: 2.6 miles round trip (moderate)
📈 Elevation Gain: 720 feet
⌛ Time Needed: 1.5-2 hours
Why It’s Epic in the Fall:
If you want a quick but spectacular fall foliage hike, Monument Mountain is a must. The short, moderately steep climb leads to unreal summit views of the Housatonic River Valley, surrounded by vivid fall colors. This hike is perfect for sunrise or sunset, when the golden light makes the leaves glow.
🍂 Must-See Highlights:
- Squaw Peak Summit – The final rocky outcrop offers an insane panoramic view of the Berkshire hills, rolling farms, and forests bursting with fall colors.
- Literary History – This is where Nathaniel Hawthorne and Herman Melville took long walks in the 1850s—allegedly inspiring Moby-Dick.
- Stunning Rock Formations – Unique granite ledges and cliffs provide amazing photo ops along the trail.
🍁 Best Time to Hike: Mid-to-late October for the best foliage at lower elevations.
🚗 Pro Tip:
- Go early in the morning or on a weekday to avoid crowds—this trail gets busy!
- Watch your footing at the summit, especially if it’s wet—there are steep drop-offs.
3. Alford Springs Reserve – The Best Hidden Gem for Fall Colors 🍃🍂
📍 Location: Alford, MA
📏 Distance: 3-5 miles round trip (moderate)
📈 Elevation Gain: 900 feet
⌛ Time Needed: 2-3 hours
Why It’s Epic in the Fall:
Tucked away near the New York border, Alford Springs is one of the most underrated fall hikes in the Berkshires. This peaceful, less-trafficked trail winds through a dense maple forest, past ancient stone walls, and up to stunning hilltop views of the Taconic Range. If you’re looking for a quiet, off-the-beaten-path hike with killer fall colors, this is your spot.
🍂 Must-See Highlights:
- Skyline Trail Viewpoint – A breathtaking overlook where you can see rolling farmland, mountain ridges, and vibrant red and gold foliage.
- Historic Stone Walls & Old Growth Forests – This area is full of New England history, with remnants of old farmsteads tucked among towering maples.
- Wildlife Spotting – Keep an eye out for hawks, deer, and even black bears, especially in the early morning or late afternoon.
🍁 Best Time to Hike: Mid-to-late October, when the entire forest glows with peak foliage.
🚗 Pro Tip:
- Bring trekking poles if you’re hiking after rain—the trail can get muddy.
- Pack a picnic—there are quiet, scenic spots to sit and enjoy the crisp autumn air.
Fall Hiking Essentials for the Berkshires:
✔️ Layers! – Mornings can be chilly, but you’ll warm up fast on the trails.
✔️ Waterproof hiking boots – Trails can be muddy and slick with fallen leaves.
✔️ A thermos of hot cider – Because fall hikes + cider = perfection 🍏🍂
✔️ A good map or offline GPS – Some trails have limited cell service.
✔️ Camera or phone – These views are too good not to capture.

Where to Find the Best Apple Cider Donuts in the Berkshires 🍩🍏
No fall trip to the Berkshires is complete without indulging in warm, cinnamon-sugar-dusted apple cider donuts. These sweet, pillowy bites of autumn perfection are made with fresh-pressed cider, delivering that perfect balance of crisp apple flavor and cozy spice. Whether you’re looking for a classic farmstand donut or something hot out of the fryer, these spots serve up the best apple cider donuts in the Berkshires.
1. Hilltop Orchards – Best Overall Experience 🌄🍩
📍 Richmond, MA
⏰ Open daily, 9 AM – 5 PM
🔗 Hilltop Orchards Website
🍎 Why You’ll Love It:
Hilltop Orchards checks every fall bucket list box—pick-your-own apples, a scenic farm setting, and of course, some of the best cider donuts in the region. Their donuts are made fresh daily using farm-pressed cider, delivering that perfectly moist and flavorful bite.
🔥 What Makes Them Special:
- Made-to-order, fresh from the fryer
- Crispy on the outside, soft and fluffy inside
- Pairs perfectly with their award-winning Johnny Mash Hard Cider 🍺
🍁 Pro Tip:
- Pair your donuts with a tasting at their onsite winery and cider mill—they make small-batch hard cider and fruit wines that scream fall.
- Go in the morning for the freshest batch and fewer crowds.
2. Bartlett’s Orchard – Best for That Classic New England Farm Feel 🚜🍂
📍 Richmond, MA
⏰ Open daily, 9 AM – 5 PM
🔗 Bartlett’s Orchard Website
🍎 Why You’ll Love It:
Bartlett’s Orchard has been a Berkshires fall staple since 1947. They crank out thousands of cider donuts daily, each one hand-rolled in cinnamon sugar for the perfect finish. If you want that warm, melt-in-your-mouth experience, this is the place.
🔥 What Makes Them Special:
- Light, airy texture with a crisp sugar coating
- Large selection of fresh apples, cider, and homemade pies
- Charming old-school farmstand atmosphere
🍁 Pro Tip:
- Grab a gallon of their fresh-pressed cider—it’s some of the best in New England.
- Their donuts sell out fast on weekends, so get there early!
3. Taft Farms – Best for Fresh, Hot Donuts 🍏🔥
📍 Great Barrington, MA
⏰ Open daily, 9 AM – 6 PM
🔗 Taft Farms Facebook
🍎 Why You’ll Love It:
If you’re looking for hot, fresh-out-of-the-fryer cider donuts, Taft Farms is your spot. This family-run farm in Great Barrington makes small-batch cider donuts throughout the day, ensuring you get them warm and irresistibly soft.
🔥 What Makes Them Special:
- Always fresh and warm – they fry up small batches all day
- Perfect balance of crispy exterior and soft inside
- Pairs beautifully with their farm-fresh hot apple cider 🍏🔥
🍁 Pro Tip:
- Weekends are prime time—they often have live music, fresh farmstand goodies, and pumpkin picking in full swing.
- Check their social media for daily updates on when hot donuts are coming out of the fryer.
Honorable Mentions – More Must-Try Cider Donuts in the Berkshires
🍏 Windy Hill Farm (Great Barrington, MA) – Small-batch donuts, pressed cider, and a gorgeous orchard to wander through.
🍏 Ioka Valley Farm (Hancock, MA) – Famous for their maple cider donuts, blending two New England flavors into one epic treat.
🍏 Lakeview Orchard (Lanesborough, MA) – A local favorite with crispy-on-the-outside, pillowy-soft-on-the-inside cider donuts.
- Thinking about visiting the Berkshires? Check out Berkshires.org – your quintessential planning guide to ensure a wonderful stay in the Berkshires!

Read next: The 11 Coolest Vacation Rentals in Massachusetts
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1 comment
[…] Just a 3-hour drive from Boston and NYC, the Berkshires of Western Massachusetts truly come alive during the autumn months. From fall foliage and charming inns to captivating art museums and exquisite farm-to-table dining, there are countless reasons to visit. Last week, I had the pleasure of exploring the Berkshires and experiencing its tight-knit community and natural serenity firsthand. During this adventure, I was captivated and inspired by the Berkshires’ eclectic character. I learned about its culture, history, and landscape, all while having the opportunity to relax and unwind. Here are 5 compelling reasons why you should visit the Berkshires this fall! Read more about the Berkshires. […]